HONG KONG — Jimmy Lai, Hong Kong’s most fiercely anti-Communist tycoon, calls himself a rebel who likes to make trouble — and he has found no shortage of it.

The owner of the city’s biggest pro-democracy publishing empire, Mr. Lai has seen his house firebombed and his company’s offices ransacked; he has been the target of an assassination plot and, recently, of multiple online attacks by what he suspects were state-sponsored hackers. On Sunday night, unidentified attackers threw Molotov cocktails at the entrances to his home and his company’s offices.

But if the protests that brought swaths of Hong Kong to a standstill throughout the autumn were partly a culmination of his decades of promoting democracy, Mr. Lai, 66, finds perhaps his greatest test in their aftermath — one that could have repercussions for media freedom in Hong Kong and Beijing’s growing intolerance of dissent in what was a British colony until 1997.

It is the kind of political street fight he has been waiting for. On the afternoon of Sept. 28, Mr. Lai was hit with fragments from a tear-gas canister — one of 87 that riot police fired that day into the crowds of protesters, mainly young students.

“We were standing there, and we saw people rush into the road and occupy it, and in that moment, I said, ‘Oh my God, this is wonderful,’ ” Mr. Lai said in a recent interview. “That was the beginning.”

Mr. Lai’s hugely popular media outlets gave blanket coverage to what followed: an 11-week siege by demonstrators camped out in three of Hong Kong’s main business and shopping districts, in what was known as Occupy Central or the Umbrella Movement. Mr. Lai was a near daily presence at the main protest encampment until he was detained with the remaining holdouts when the police cleared the site on Dec. 11.

Now, Mr. Lai’s fight looks set to shift from the streets to the courts. Outraged by what has been branded at best an illegal assembly and at worst an affront to China’s sovereignty over the territory, the authorities in Hong Kong have been preparing formal charges against scores of people they have identified as the main figures in the Occupy protests. On Friday, Mr. Lai was instructed to report to police headquarters on Jan. 21.

“It’s going to be very interesting to see whether he is going to bear the heaviest weight as the blackest ‘black hand,’ ” said Michael DeGolyer, a professor of political economy at Hong Kong Baptist University, who runs a series of polls on democracy. Black hand is a term the Chinese authorities have used to refer to those who stir up antigovernment activity.

“You could argue that he was perhaps the most significant supporter of Occupy Central, in terms of providing it a platform” through his media outlets, Mr. DeGolyer added. “We’re going to have a significant freedom of the press issue here, which is going to tell us a great deal about Hong Kong’s future.”

Separately, Hong Kong’s anticorruption agency has been investigating Mr. Lai’s long-running donations to the city’s pro-democracy politicians and their parties. The investigation followed public complaints after emails detailing some of the donations were leaked in the summer, a result of hacking attacks on Mr. Lai’s company, Next Media Ltd. He has said the attacks appeared to have been state sponsored.

“Since the case is on, I better keep my mouth shut,” Mr. Lai said. “But I think whatever comes, I will take it. I’m not worried about this, because I don’t think I’ve done anything wrong.”

Mr. Lai’s path to the publishing business was an unlikely one. He was born in Guangzhou, a city in southern China, to a wealthy family that lost everything when the Communists took power in 1949. The family paid a smuggler to take him by boat to Hong Kong in 1960 at age 12. He began working and sleeping in one of the city’s then numerous sweatshops, making knitwear.

He did odd jobs at first, then became a knitter. He taught himself English along the way, enough to land a job as an office clerk at a trading firm in Central, the main business district. By the time Mr. Lai was 27, he and two partners had started their own small clothing factory, which by the late 1980s had grown into Hong Kong’s first “fast fashion” retail chain, Giordano.

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Jimmy Lai being taken away by police officers near Hong Kong government offices in the Admiralty district on Dec. 11.CreditAthit Perawongmetha/Reuters

When student protesters flooded the streets of Beijing in democracy demonstrations in the spring of 1989, Giordano did a brisk business in Hong Kong selling T-shirts printed with the slogan “The dynasty is dead, please step down” in big, red Chinese characters. After the Chinese government ordered a military crackdown in and around Tiananmen Square on June 4, 1989, killing hundreds, possibly thousands, Mr. Lai’s politics hardened further.

He decided to branch into media, starting Next Magazine the next year. The magazine divided its coverage between serious muckraking investigations and paparazzi-style exposés of the private lives of local celebrities.

Mr. Lai’s weekly column in Next, which he still writes, took aim at the Chinese leadership in Beijing. One article in July 1994 repeatedly insulted Li Peng, the prime minister — who was seen as a driving force behind the 1989 military crackdown — and told him to “drop dead.”

Within weeks, the authorities began closing Giordano stores in mainland China, the fastest-growing market for Mr. Lai’s retail chain. Before long, Mr. Lai decided he had no choice but to sell the business.

“I was naïve. Not that I expected something like this was going to happen, but neither did I expect it was going to be smooth sailing for my career in China,” Mr. Lai said. “If I really treated business like a businessman, I wouldn’t have done what I have done — opposing China. No businessman in their right mind would do this, because you know that there will be repercussions.”

Mr. Lai used money from the sale of Giordano to invest further in media. In 1995 he started a newspaper, Apple Daily, which quickly became one of the biggest in Hong Kong. He then moved into Taiwan’s much-larger media market, starting a Taiwanese edition of Next Magazine in 2001 and of Apple Daily in 2003. He later set up an animated news unit in Taiwan, Next Media Animation.

The influence Mr. Lai wields in Hong Kong’s media and democratic political circles has drawn many detractors over the years.

Michael Tien, a pro-Beijing legislator and a delegate to China’s National People’s Congress, said Mr. Lai’s role as the main opposition media figure in Hong Kong, combined with his role as a financial backer of protest movements, benefits him financially because it sells newspapers.

“He makes the money, and he uses the money to support the anti-establishment movement, and that creates more noise, and sells more papers. That’s the game he’s playing,” said Mr. Tien, who also founded a chain of clothing stores, G2000, that competes against Giordano.

Even within Hong Kong’s democracy movement, which is increasingly being led by a younger generation, the dominance in print, online and mobile news of Mr. Lai’s publications can create unease.

Mr. Lai “has played a very important role in Hong Kong’s democratic movement, as his media has always been on the side of democracy,” Joshua Wong, an 18-year-old student protest leader, said by phone on Sunday. Still, Mr. Wong said, “Hong Kong’s democratic movement can’t just rely on one media outlet.”

“It’s unhealthy, and it even risks being controlled by one publication,” he continued.

“The more I’m in the front of the movement, the less appropriate that I should be so closely connected with our media,” he said. “You cannot have the media so close to you that it becomes your voice. This is no good, because it becomes too extreme and people will resent it.”

Mr. Lai says he can see the day, maybe in 10 years, when print will cease to be economically viable and his publications will switch to digital platforms. He still owns 73.5 percent of Next Media and says he is adamantly against selling it. Unlike many Chinese businessmen, he has no plans to hand off the business to any of his six children, who range in age from 8 to 37.

“I don’t think I should ask my kids to inherit my business, because they can’t start where I did,” he said. “I was from the street. I’m a very different make of person. I’ve been a fighter all my life.”